메뉴 건너뛰기




Volumn 34, Issue 5, 2006, Pages 1540-1551

Synthesis and characterization of oligonucleotides containing 2′-fluorinated thymidine glycol as inhibitors of the endonuclease III reaction

Author keywords

[No Author keywords available]

Indexed keywords

5' O (4,4' DIMETHOXYTRITYL) 3' O BENZOYL 2' FLUOROTHYMIDINE; 5' O (4,4' DIMETHOXYTRITYL) 3' O BENZOYL 5,6 DIHYDRO 5,6 DI[(TERT BUTYL)DIMETHYLSILYLOXYL] 2' FLUOROTHYMIDINE; 5' O (4,4' DIMETHOXYTRITYL) 3' O BENZOYL 5,6 DIHYDRO 5,6 DIHDROXY 2' FLUOROTHYMIDINE; 5' O (4,4' DIMETHOXYTRITYL) 5,6 DIHYDRO 5,6 DI[(TERT BUTYL)DIMETHYLSILYLOXYL] 2' FLUOROTHYMIDINE; 5' O (4,4' DIMETHOXYTRITYL) 5,6 DIHYDRO 5,6 DI[(TERT BUTYL)DIMETHYLSILYLOXYL] 2' FLUOROTHYMIDINE 3' [(2 CYANOETHYL) N,N DIISOPROPYL]PHOSPHORAMIDITE; ENDONUCLEASE; ENDONUCLEASE III; OLIGONUCLEOTIDE; THYMIDINE DERIVATIVE; UNCLASSIFIED DRUG; 1 (2 DEOXY 2 FLUORORIBOFURANOSYL) 5,6 DIHYDRO 5,6 DIHYDROXYTHYMINE; 1-(2-DEOXY-2-FLUORORIBOFURANOSYL)-5,6-DIHYDRO-5,6-DIHYDROXYTHYMINE; DEOXYRIBONUCLEASE (PYRIMIDINE DIMER); DRUG DERIVATIVE; ENDONUCLEASE V, PHAGE T4; ENZYME INHIBITOR; ESCHERICHIA COLI PROTEIN; NTH PROTEIN, E COLI; ORGANOPHOSPHORUS COMPOUND; PHOSPHORAMIDOUS ACID; THYMIDINE; VIRUS PROTEIN;

EID: 33645531920     PISSN: 03051048     EISSN: 13624962     Source Type: Journal    
DOI: 10.1093/nar/gkl061     Document Type: Article
Times cited : (21)

References (31)
  • 1
    • 0018926091 scopus 로고
    • DNA N-glycosylases and UV repair
    • Demple,B. and Linn,S. (1980) DNA N-glycosylases and UV repair. Nature, 287, 203-208.
    • (1980) Nature , vol.287 , pp. 203-208
    • Demple, B.1    Linn, S.2
  • 3
    • 0030890419 scopus 로고    scopus 로고
    • Cloning and expression of the cDNA encoding the human homologue of the DNA repair enzyme, Escherichia coli endonuclease III
    • Hilbert,T.P., Chaung,W., Boorstein,R.J., Cunningham,R.P. and Teebor,G.W. (1997) Cloning and expression of the cDNA encoding the human homologue of the DNA repair enzyme, Escherichia coli endonuclease III. J. Biol. Chem., 272, 6733-6740.
    • (1997) J. Biol. Chem. , vol.272 , pp. 6733-6740
    • Hilbert, T.P.1    Chaung, W.2    Boorstein, R.J.3    Cunningham, R.P.4    Teebor, G.W.5
  • 4
    • 0032555571 scopus 로고    scopus 로고
    • Purification and characterization of human NTH1, a homolog of Escherichia coli endonuclease III: Direct identification of Lys-212 as the active nucleophilic residue
    • Ikeda,S., Biswas,T., Roy,R., Izumi,T., Boldogh,I., Kurosky,A., Sarker,A.H., Seki,S. and Mitra,S. (1998) Purification and characterization of human NTH1, a homolog of Escherichia coli endonuclease III: Direct identification of Lys-212 as the active nucleophilic residue. J. Biol. Chem., 273, 21585-21593.
    • (1998) J. Biol. Chem. , vol.273 , pp. 21585-21593
    • Ikeda, S.1    Biswas, T.2    Roy, R.3    Izumi, T.4    Boldogh, I.5    Kurosky, A.6    Sarker, A.H.7    Seki, S.8    Mitra, S.9
  • 5
    • 0027366974 scopus 로고
    • Substrate specificity of the Escherichia coli endonuclease III: Excision of thymine- and cytosine-derived lesions in DNA produced by radiation-generated free radicals
    • Dizdaroglu,M., Laval,J. and Boiteux,S. (1993) Substrate specificity of the Escherichia coli endonuclease III: Excision of thymine- and cytosine-derived lesions in DNA produced by radiation-generated free radicals. Biochemistry, 32, 12105-12111.
    • (1993) Biochemistry , vol.32 , pp. 12105-12111
    • Dizdaroglu, M.1    Laval, J.2    Boiteux, S.3
  • 6
    • 0028305721 scopus 로고
    • New substrates for old enzymes. 5-Hydroxy-2′-deoxycytidine and 5-hydroxy-2′-deoxyuridine are substrates for Escherichia coli endonuclease III and formamidopyrimidine DNA N-glycosylase, while 5-hydroxy-2′-deoxyuridine is a substrate for uracil DNA N-glycosylase
    • Hatahet,Z., Kow,Y.W., Purmal,A.A., Cunningham,R.P. and Wallace,S.S. (1994) New substrates for old enzymes. 5-Hydroxy-2′-deoxycytidine and 5-hydroxy-2′-deoxyuridine are substrates for Escherichia coli endonuclease III and formamidopyrimidine DNA N-glycosylase, while 5-hydroxy-2′-deoxyuridine is a substrate for uracil DNA N-glycosylase. J. Biol. Chem., 269, 18814-18820.
    • (1994) J. Biol. Chem. , vol.269 , pp. 18814-18820
    • Hatahet, Z.1    Kow, Y.W.2    Purmal, A.A.3    Cunningham, R.P.4    Wallace, S.S.5
  • 7
    • 0021331957 scopus 로고
    • DNA glycosylase activities for thymine residues damaged by ring saturation, fragmentation, or ring contraction are functions of endonuclease III in Escherichia coli
    • Breimer,L.H. and Lindahl,T. (1984) DNA glycosylase activities for thymine residues damaged by ring saturation, fragmentation, or ring contraction are functions of endonuclease III in Escherichia coli. J. Biol. Chem., 259, 5543-5548.
    • (1984) J. Biol. Chem. , vol.259 , pp. 5543-5548
    • Breimer, L.H.1    Lindahl, T.2
  • 8
    • 0023710309 scopus 로고
    • Excision repair of thymine glycols, urea residues, and apurinic sites in Escherichia coli
    • Laspia,M.F. and Wallace,S.S. (1988) Excision repair of thymine glycols, urea residues, and apurinic sites in Escherichia coli. J. Bacteriol., 170, 3359-3366.
    • (1988) J. Bacteriol. , vol.170 , pp. 3359-3366
    • Laspia, M.F.1    Wallace, S.S.2
  • 9
    • 0035339684 scopus 로고    scopus 로고
    • Repair of hydantoins, one electron oxidation product of 8-oxoguanine, by DNA glycosylases of Escherichia coli
    • Hazra,T.K., Muller,J.G., Manuel,R.C., Burrows,C.J., Lloyd,R.S. and Mitra,S. (2001) Repair of hydantoins, one electron oxidation product of 8-oxoguanine, by DNA glycosylases of Escherichia coli. Nucleic Acids Res., 29, 1967-1974.
    • (2001) Nucleic Acids Res. , vol.29 , pp. 1967-1974
    • Hazra, T.K.1    Muller, J.G.2    Manuel, R.C.3    Burrows, C.J.4    Lloyd, R.S.5    Mitra, S.6
  • 10
    • 0035339557 scopus 로고    scopus 로고
    • Escherichia coli Nth and human hNTH1 DNA glycosylases are involved in removal of 8-oxoguanine from 8-oxoguanine/guanine mispairs in DNA
    • Matsumoto,Y., Zhang,Q.M., Takao,M., Yasui,A. and Yonei,S. (2001) Escherichia coli Nth and human hNTH1 DNA glycosylases are involved in removal of 8-oxoguanine from 8-oxoguanine/guanine mispairs in DNA. Nucleic Acids Res., 29, 1975-1981.
    • (2001) Nucleic Acids Res. , vol.29 , pp. 1975-1981
    • Matsumoto, Y.1    Zhang, Q.M.2    Takao, M.3    Yasui, A.4    Yonei, S.5
  • 12
    • 0026075807 scopus 로고
    • Reductive methylation of the amino terminus of endonuclease V eradicates catalytic activities: Evidence for an essential role of the amino terminus in the chemical mechanisms of catalysis
    • Schrock,R.D. and Lloyd,R.S. (1991) Reductive methylation of the amino terminus of endonuclease V eradicates catalytic activities: Evidence for an essential role of the amino terminus in the chemical mechanisms of catalysis. J. Biol. Chem., 266, 17631-17639.
    • (1991) J. Biol. Chem. , vol.266 , pp. 17631-17639
    • Schrock, R.D.1    Lloyd, R.S.2
  • 13
    • 0027301692 scopus 로고
    • Evidence for an imino intermediate in the T4 endonuclease V reaction
    • Dodson,M.L., Schrock,R.D. and Lloyd,R.S. (1993) Evidence for an imino intermediate in the T4 endonuclease V reaction. Biochemistry, 32, 8284-8290.
    • (1993) Biochemistry , vol.32 , pp. 8284-8290
    • Dodson, M.L.1    Schrock, R.D.2    Lloyd, R.S.3
  • 14
    • 0029132769 scopus 로고
    • Studies on the catalytic mechanism of five DNA glycosylases: Probing for enzyme-DNA imino intermediates
    • Sun,B., Latham,K.A., Dodson,M.L. and Lloyd,R.S. (1995) Studies on the catalytic mechanism of five DNA glycosylases: Probing for enzyme-DNA imino intermediates. J. Biol. Chem., 270, 19501-19508.
    • (1995) J. Biol. Chem. , vol.270 , pp. 19501-19508
    • Sun, B.1    Latham, K.A.2    Dodson, M.L.3    Lloyd, R.S.4
  • 15
    • 0037925462 scopus 로고    scopus 로고
    • Structure of a trapped endonuclease III-DNA covalent intermediate
    • Fromme,J.C. and Verdine,G.L. (2003) Structure of a trapped endonuclease III-DNA covalent intermediate. EMBO J., 22, 3461-3471.
    • (2003) EMBO J. , vol.22 , pp. 3461-3471
    • Fromme, J.C.1    Verdine, G.L.2
  • 16
    • 0028904903 scopus 로고
    • Reaction mechanism of T4 endonuclease V determined by analysis using modified oligonucleotide duplexes
    • Iwai,S., Maeda,M., Shirai,M., Shimada,Y., Osafune,T., Murata,T. and Ohtsuka,E. (1995) Reaction mechanism of T4 endonuclease V determined by analysis using modified oligonucleotide duplexes. Biochemistry, 34, 4601-4609.
    • (1995) Biochemistry , vol.34 , pp. 4601-4609
    • Iwai, S.1    Maeda, M.2    Shirai, M.3    Shimada, Y.4    Osafune, T.5    Murata, T.6    Ohtsuka, E.7
  • 17
    • 0028863468 scopus 로고
    • Atomic model of a pyrimidine dimer excision repair enzyme complexed with a DNA substrate: Structural basis for damaged DNA recognition
    • Vassylyev,D.G., Kashiwagi,T., Mikami,Y., Ariyoshi,M., Iwai,S., Ohtsuka,E. and Morikawa,K. (1995) Atomic model of a pyrimidine dimer excision repair enzyme complexed with a DNA substrate: Structural basis for damaged DNA recognition. Cell, 83, 773-782.
    • (1995) Cell , vol.83 , pp. 773-782
    • Vassylyev, D.G.1    Kashiwagi, T.2    Mikami, Y.3    Ariyoshi, M.4    Iwai, S.5    Ohtsuka, E.6    Morikawa, K.7
  • 18
    • 0034602037 scopus 로고    scopus 로고
    • Synthesis of thymine glycol containing oligonucleotides from a building block with the oxidized base
    • Iwai,S. (2000) Synthesis of thymine glycol containing oligonucleotides from a building block with the oxidized base. Angew. Chem. Int. Ed., 39, 3874-3876.
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 3874-3876
    • Iwai, S.1
  • 19
    • 0035887431 scopus 로고    scopus 로고
    • Synthesis and thermodynamic studies of oligonucleotides containing the two isomers of thymine glycol
    • Iwai,S. (2001) Synthesis and thermodynamic studies of oligonucleotides containing the two isomers of thymine glycol. Chem. Eur. J., 7, 4343-4351.
    • (2001) Chem. Eur. J. , vol.7 , pp. 4343-4351
    • Iwai, S.1
  • 21
    • 0542405231 scopus 로고
    • Nucleosides XLIX. Nuclear magnetic resonance studies of 2′- and 3′-halogeno nucleosides. The conformations of 2′-deoxy-2′-fluorouridine and 3′-deoxy-3′-fluoro-β-D-arabinofuranosyluracil. Can. J. Chem.
    • Cushley,R.J., Codington,J.F. and Fox,J.J. (1968) Nucleosides XLIX. Nuclear magnetic resonance studies of 2′- and 3′-halogeno nucleosides. The conformations of 2′-deoxy-2′-fluorouridine and 3′-deoxy-3′-fluoro-β-D-arabinofuranosyluracil. Can. J. Chem., 46, 1131-1140.
    • (1968) , vol.46 , pp. 1131-1140
    • Cushley, R.J.1    Codington, J.F.2    Fox, J.J.3
  • 22
    • 0016291368 scopus 로고
    • Nucleoside conformations 16. Nuclear magnetic resonance and circular dichroism studies on pyrimidine-2′-fluoro-2′-deoxyribonucleosides
    • Blandin,M., Son,T.D., Catlin,J.C. and Guschlbauer,W. (1974) Nucleoside conformations 16. Nuclear magnetic resonance and circular dichroism studies on pyrimidine-2′-fluoro-2′-deoxyribonucleosides. Biochim. Biophys. Acta, 361, 249-256.
    • (1974) Biochim. Biophys. Acta , vol.361 , pp. 249-256
    • Blandin, M.1    Son, T.D.2    Catlin, J.C.3    Guschlbauer, W.4
  • 23
    • 0016268802 scopus 로고
    • X-ray structure of 3′,5′-diacetyl-2′-deoxy-2′-fluorouridine: A pyrimidine nucleoside in the syn conformation
    • Suck,D., Saenger,W., Main,P., Germain,G. and Declercq,J.P. (1974) X-ray structure of 3′,5′-diacetyl-2′-deoxy-2′-fluorouridine: A pyrimidine nucleoside in the syn conformation. Biochim. Biophys. Acta, 361, 257-265.
    • (1974) Biochim. Biophys. Acta , vol.361 , pp. 257-265
    • Suck, D.1    Saenger, W.2    Main, P.3    Germain, G.4    Declercq, J.P.5
  • 24
    • 0019332380 scopus 로고
    • Nucleoside conformation is determined by the electronegativity of the sugar substituent
    • Guschlbauer,W. and Jankowski,K. (1980) Nucleoside conformation is determined by the electronegativity of the sugar substituent. Nucleic Acids Res., 8, 1421-1433.
    • (1980) Nucleic Acids Res. , vol.8 , pp. 1421-1433
    • Guschlbauer, W.1    Jankowski, K.2
  • 25
    • 0028292447 scopus 로고
    • Removal of t-butyldimethylsilyl protection in RNA-synthesis. Triethylamine trihydrofluoride (TEA, 3HF) is a more reliable alternative to tetrabutylammonium fluoride (TBAF)
    • Westman,E. and Stromberg,R. (1994) Removal of t-butyldimethylsilyl protection in RNA-synthesis. Triethylamine trihydrofluoride (TEA, 3HF) is a more reliable alternative to tetrabutylammonium fluoride (TBAF). Nucleic Acids Res., 22, 2430-2431.
    • (1994) Nucleic Acids Res. , vol.22 , pp. 2430-2431
    • Westman, E.1    Stromberg, R.2
  • 26
    • 0026760983 scopus 로고
    • Synthesis of the diastereomers of thymidine glycol, determination of concentrations and rates of interconversion of their cis-trans epimers at equilibrium and demonstration of differential alkali lability within DNA
    • Lustig,M.J., Cadet,J., Boorstein,R.J. and Teebor,G.W. (1992) Synthesis of the diastereomers of thymidine glycol, determination of concentrations and rates of interconversion of their cis-trans epimers at equilibrium and demonstration of differential alkali lability within DNA. Nucleic Acids Res., 20, 4839-4845.
    • (1992) Nucleic Acids Res. , vol.20 , pp. 4839-4845
    • Lustig, M.J.1    Cadet, J.2    Boorstein, R.J.3    Teebor, G.W.4
  • 29
    • 1842638748 scopus 로고    scopus 로고
    • Differential specificity of human and Escherichia coli endonuclease III and VIII homologues for oxidative base lesions
    • Katafuchi,A., Nakano,T., Masaoka,A., Terato,H., Iwai,S., Hanaoka,F. and Ide,H. (2004) Differential specificity of human and Escherichia coli endonuclease III and VIII homologues for oxidative base lesions. J. Biol. Chem., 279, 14464-14471.
    • (2004) J. Biol. Chem. , vol.279 , pp. 14464-14471
    • Katafuchi, A.1    Nakano, T.2    Masaoka, A.3    Terato, H.4    Iwai, S.5    Hanaoka, F.6    Ide, H.7
  • 30
    • 0034613265 scopus 로고    scopus 로고
    • Gelonin is an unusual DNA glycosylase that removes adenine from single-stranded DNA, normal base pairs and mismatches
    • Nicolas,E., Beggs,J.M. and Taraschi,T.F. (2000) Gelonin is an unusual DNA glycosylase that removes adenine from single-stranded DNA, normal base pairs and mismatches. J. Biol. Chem., 275, 31399-31406.
    • (2000) J. Biol. Chem. , vol.275 , pp. 31399-31406
    • Nicolas, E.1    Beggs, J.M.2    Taraschi, T.F.3
  • 31
    • 0028181135 scopus 로고
    • α-Deoxyadenosine, a major anoxic radiolysis product of adenine in DNA, is a substrate for Escherichia coli endonuclease IV
    • Ide,H., Tedzuka,K., Shimizu,H., Kimura,Y., Purmal,A.A., Wallace,S.S. and Kow,Y.W. (1994) α-Deoxyadenosine, a major anoxic radiolysis product of adenine in DNA, is a substrate for Escherichia coli endonuclease IV. Biochemistry, 33, 7842-7847.
    • (1994) Biochemistry , vol.33 , pp. 7842-7847
    • Ide, H.1    Tedzuka, K.2    Shimizu, H.3    Kimura, Y.4    Purmal, A.A.5    Wallace, S.S.6    Kow, Y.W.7


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.